5-Acetylamino-2-allyl-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid

ID: ALA2112793

PubChem CID: 71450895

Max Phase: Preclinical

Molecular Formula: C14H23NO8

Molecular Weight: 333.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC[C@]1(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H](C(O)C(O)CO)O1

Standard InChI:  InChI=1S/C14H23NO8/c1-3-4-14(13(21)22)5-8(18)10(15-7(2)17)12(23-14)11(20)9(19)6-16/h3,8-12,16,18-20H,1,4-6H2,2H3,(H,15,17)(H,21,22)/t8-,9?,10+,11?,12+,14+/m0/s1

Standard InChI Key:  IUGVDRFIVSPVGO-XQFMPKBFSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    1.7417   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -3.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -4.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -7.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -3.8667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0333   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7375   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -3.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458   -2.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -7.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -3.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -6.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -8.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -9.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -9.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  6  7  1  0
  7  3  1  0
  4  8  1  1
  3  9  1  1
 10  9  1  0
 11  5  1  0
 12  8  2  0
 13 10  2  0
 14 17  1  0
 15 14  2  0
 16  5  1  0
 17  4  1  0
 18  8  1  0
  7 19  1  6
 20 11  1  0
 21 22  1  0
 22 11  1  0
 23 10  1  0
  6  4  1  0
  1  5  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2112793

   (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-prop-2-enyl-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 333.34

Molecular Weight (Monoisotopic): 333.1424

AlogP: -2.25

#Rotatable Bonds: 7

Polar Surface Area: 156.55

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.68

CX Basic pKa: ┄

CX LogP: -2.64

CX LogD: -5.95

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.29

Np Likeness Score: 1.47

References

1. Nagy JO, Wang P, Gilbert JH, Schaefer ME, Hill TG, Callstrom MR, Bednarski MD..  (1992)  Carbohydrate materials bearing neuraminidase-resistant C-glycosides of sialic acid strongly inhibit the in vitro infectivity of influenza virus.,  35  (23): [PMID:1447751] [10.1021/jm00101a031]

Source

Source(1):

• Scientific Literature